title: Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment.
abstract: A new practical synthesis of alpha-GalCer and of its analogues is presented, opening the chance to easily modify the sphingosine chain. The common precursor is a disaccharide, obtained by coupling tetra-O-benzyl-D-galactose with allyl 2,3-O-isopropylidene-D-lyxofuranoside. Introduction of alkyl chains via Wittig reaction (for alpha-GalCer and OCH) or via Williamson reaction (for oxa analogues) followed by standard synthetic steps allows one to efficiently obtain such compounds. The analogues are able to activate iNKT cells when presented by CD1d expressing cells.
authors.affiliation: Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale Amedeo Avogadro, via Bovio 6, 28100 Novara, Italy.
authors.forename: Mario
authors.initials: M
authors.lastname: Michieletti
authors.forename: Antonio
authors.initials: A
authors.lastname: Bracci
authors.forename: Federica
authors.initials: F
authors.lastname: Compostella
authors.forename: Gennaro
authors.initials: G
authors.lastname: De Libero
authors.forename: Lucia
authors.initials: L
authors.lastname: Mori
authors.forename: Silvia
authors.initials: S
authors.lastname: Fallarini
authors.forename: Grazia
authors.initials: G
authors.lastname: Lombardi
authors.forename: Luigi
authors.initials: L
authors.lastname: Panza
mesh_terms: D004187:Disaccharides / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D006825:Hybridomas / Q000276:immunology / Q000378:metabolism / Q000473:pathology; D007376:Interleukin-2 / Q000378:metabolism; D055611:Natural Killer T-Cells / Q000187:drug effects / Q000378:metabolism; D013110:Sphingosine / Q000737:chemistry
chemical_list: D004187:Disaccharides; D005699:Galactosylceramides; D007376:Interleukin-2; D013110:Sphingosine; C103873:KRN 7000